Guide to Spring Classics Road Bike Racing

Milano–San Remo (Milan–San Remo)

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Nickname: La Classicissima, La Primavera

How to say it: “mee-lano sahn ray-mo”

The first of cycling’s monuments, a distinction given to only five of the sport’s longest, oldest, and most difficult races, Milan–San Remo is also by far the longest at a whopping 298 kilometers. First organized by the Italian sports newspaper La Gazetta dello Sport in 1907, Italian riders have won the race 50 times, the last being Filippo Pozzato in 2006. Belgium is la Classicissima’s next most successful country; Eddy Merckx holds the record with seven wins while Roger de Vlaeminck has three. No North American has ever won Milan-San Remo, although the United Kingdom and Ireland have each won two—Mark Cavendish most recently, in 2009.

The first 250 kilometers of the race hold few difficulties; organizers have tried adding climbs earlier in the event, but they do little to affect the outcome as they come too far from the finale to matter. In the end, Milan–San Remo always comes down to two climbs: the Cipressa (chee-prrray-sah) and the Poggio (po-ji-oh).

The Cipressa usually splits the race into two or three groups, with a small breakaway of riders escaping from the front and a larger group of sprinters doing their best to stay in contention at the back. The race usually comes back together just in time for the race’s final wall of the Poggio, a steep, twisty little climb with a descent that favors those willing to risk their lives on its tight hairpins. This is the last chance for a breakaway to survive, and you’ll see many bury themselves to try and make one stick. Should they fail, any surviving sprinters will look to take the season’s first major win along the Italian Riviera.